Methods and intermediates for the synthesis of dipyrrin-substituted porphyrinic macrocycles
AssigneeNorth Carolina State University
InventorsLianhe Yu, Kannan Muthukumaran, Prathapan Sreedharan, Jonathan Lindsey
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Abstract
The present invention provides dipyrrin substituted porphyrinic macrocycles, intermediates useful for making the same, and methods of making the same. Such compounds may be used for purposes including the making of molecular memory devices, solar cells and light harvesting arrays.
Claims33
1-6. (canceled)
A method of disassembling a bis(dipyrrinato)metal complex to produce separate dipyrrin groups, comprising:
- reacting a bis(dipyrrinato)metal complex with a thiol reagent under neutral conditions to disassemble said bis(dipyrrinato) metal complex into separate dipyrrin groups.
A method of synthesizing a dipyrrin-substituted porphyrinic macrocycle, comprising:
- (a) coupling a porphyrinic macrocycle and a bis(dipyrrinato)metal complex to form a reaction product;
- and then
- (b) treating said reaction product with a thiol reagent to disassemble said reaction product and form said dipyrrin-substituted porphyrinic macrocycle.
A method of synthesizing a dipyrrin-substituted porphyrinic macrocycle, comprising:
- condensing a dipyrromethane-dicarbinol with a dipyrrin-substituted dipyrromethane in a weakly polar solvent in the presence of a Lewis acid to produce a dipyrrin-substituted porphyrinic macrocycle.
A method of synthesizing a trans-(dipyrrin)2-porphyrinic macrocycle, comprising:
- reacting a dipyrrin-carboxaldehyde with a dipyrromethane in the presence of an acid catalyst to produce said trans-(dipyrrin)2-porphyrinic macrocycle.
A porphyrinic macrocycle having from 1 to 4 dipyrrins substituted thereon.
A polymer comprising a plurality of linked porphyrinic macrocycles, at least one of said porphyrinic macrocycles having from 1 to 4 dipyrrins substituted thereon.
A sandwich coordination compound of the formula LnMn-1, where each L is an independently selected heterocyclic ligand, each M is a metal, n is 2 or 3, and at least one of said heterocyclic ligand is a porphyrinic macrocycles having from 1 to 4 dipyrrins substituted thereon.
An apparatus for storing data, said apparatus comprising a fixed electrode electrically coupled to a storage medium, said storage medium comprising a porphyrinic macrocycle having from 1 to 4 dipyrrins substituted thereon.
A light harvesting array, comprising:
- (a) a first substrate comprising a first electrode;
- and (b) a layer of light harvesting rods electrically coupled to the first electrode, each of the light harvesting rods comprising a polymer of Formula I:
- wherein:
- m is at least 1;
- X1 is a charge separation group having an excited-state of energy equal to or lower than that of X2;
- X2 through Xm+1 are chromophores, and at least one of said chromophores comprises a porphyrinic macrocycle having from 1 to 4 dipyrrins substituted thereon.
Dependencies are inferred from the claim text.